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维生素E侧链—异植物醇合成工艺研究

Synthesis of Isophytol-side Chain of Vitamin E

【作者】 陈刚

【导师】 李勤耕;

【作者基本信息】 重庆医科大学 , 药物化学, 2014, 硕士

【摘要】 目的:改进异植物醇合成工艺。方法:以丙酮为起始原料,与氯乙烯经过格氏反应得到2-甲基-3-丁烯-2-醇,再与乙酰乙酸甲酯经过Carroll重排得到甲基庚烯酮,再经过两次相同的格氏反应和Carroll重排得到法尼基丙酮,然后还原得到六氢法尼基丙酮,最后再经格氏反应得到异植物醇。结果:目标产物和关键中间体经MS谱,1H-NMR谱等确证了结构。结论:改进后的工艺路线生产设备简单,条件温和,收率高(总收率64.4%),适合大规模化生产。

【Abstract】 Objective: To improve synthesis of isophytol.Methods: Acetone, the starting material, reacted with vinyl chloride toobtain2-Methyl-3-butene-2-ol by Grignard reaction, and then reacted withmethyl acetoacetate to form methyl heptenone by Carroll rearrangement,followed by double similar procedures to give farnesylacetone.Subsequently, hexahydro-farnesylacetone was prepared by catalytichydrogenation at the presence of Pd/C. Finally, isophytol was obtained byGrignard reaction again.Results: The target compound and key intermediates were confirmedby MS and1H-NMR.Conclusion: The improved synthesis will benefit from simpleequipment, mild conditions, high yield (the total yield of64.4%) and couldbe readily scale-up to mass production.

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